Imidazole → HCID 20206233, compound

HRID 1380301Notes

Reaction equation

HRID 1380301 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1F)[C:12]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])=[O:13]>CN(C)C=O>[Cl:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[C:12]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])=[O:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 20206227HCID 20206227, compound

Product 1

HCID 20206233HCID 20206233, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2.3 g of sodium hydride (60% dispersion in mineral oil) in 50 ml of dimethylformamide is added 4.2 g of imidazole over a 5 minute period under occasional ice cooling. After stirring at room temperature for 30 minutes, a solution of 14.2 g of 3-chloro-4-fluoro-2',4',6'-trimethylbenzophenone in 10 ml of dimethylformamide is added and the mixture is stirred at 50° C. for 3 hours. The reaction mixture is poured into ice-cold water and extracted with benzene. After benzene is distilled off, the residue is purified column-chromatographically to give 15.6 g of 3-chloro-4-(1-imidazolyl)-2',4',6'-trimethylbenzophenone as a colorless oil.

Workup

  1. stirringthe mixture is stirred at 50° C. for 3 hours
  2. additionThe reaction mixture is poured into ice-cold water
  3. extractionextracted with benzene
  4. distillationAfter benzene is distilled off
  5. customthe residue is purified column-chromatographically

Sources & evidence

ORD record
ord-6b634817710347fb90bd7d48fb2cf2d1
Source dataset
uspto-grants-1986_04
Patent number
US04581369

Reaction notes

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